Tris(chloropropyl) phosphate
{{Chembox
| ImageFile = TCPP.svg
| ImageAlt =
| IUPACName = Tris(2-chloro-1-methylethyl) phosphate
| OtherNames = {{bulleted list|Tris(1-chloro-2-propyl)phosphate|Tris(2-chloroisopropyl)phosphate|Tris(monochloroisopropyl) phosphate (TMCP)|
Tris(2-chloroisopropyl) phosphate (TCIP)}}
| Section1 = {{Chembox Identifiers
| CASNo = 13674-84-5
| ChEBI = 143728
| ChEMBL = 3188873
| ChemSpiderID = 24387
| EC_number = 237-158-7
| PubChem = 26176
| UNII = CRT22GFY70
| StdInChI=1S/C9H18Cl3O4P/c1-7(4-10)14-17(13,15-8(2)5-11)16-9(3)6-12/h7-9H,4-6H2,1-3H3
| StdInChIKey = KVMPUXDNESXNOH-UHFFFAOYSA-N
| SMILES = O=P(OC(CCl)C)(OC(CCl)C)OC(CCl)C
}}
| Section2 = {{Chembox Properties
|C=9 | H=18 | Cl=3| O=4 | P=1
| Appearance = Liquid
| Density =
| MeltingPtC = 20
| BoilingPtC = 290
| BoilingPt_notes= decomposes
| Solubility = 1,080 mg/l at 20°C
}}
| Section3 = {{Chembox Hazards
| FlashPt =
| AutoignitionPt =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|H302}}
| PPhrases = {{P-phrases|264|270|301+312|330}}
}}
}}
Tris(chloropropyl) phosphate (commonly abbreviated TCPP) is a chlorinated organophosphate flame retardant commonly added to polyurethane foams.{{cite journal |last1=Yadav |first1=Anilkumar |last2=de Souza |first2=Felipe M. |last3=Dawsey |first3=Tim |last4=Gupta |first4=Ram K. |title=Recent Advancements in Flame-Retardant Polyurethane Foams: A Review |journal=Industrial & Engineering Chemistry Research |date=19 October 2022 |volume=61 |issue=41 |pages=15046–15065 |doi=10.1021/acs.iecr.2c02670|s2cid=252832072 }} Comparatively minor amounts are used in PVC and EVA.{{cite web |title=European Union Risk Assessment Report: TCPP |url=https://echa.europa.eu/documents/10162/8a6e5c7c-15d6-4e80-b083-0cca700c32d3 |publisher=ECHA |access-date=1 March 2024}}
Synthesis
TCPP is prepared industrially by the reaction of propylene oxide with phosphoryl chloride. In practise this produces a range of products, of which the tris(2-chloro-1-methylethyl) isomer tends to dominate (50-85% w/w).{{cite journal |last1=Truong |first1=Jimmy W. |last2=Diamond |first2=Miriam L. |last3=Helm |first3=Paul A. |last4=Jantunen |first4=Liisa M. |title=Isomers of tris(chloropropyl) phosphate (TCPP) in technical mixtures and environmental samples |journal=Analytical and Bioanalytical Chemistry |date=December 2017 |volume=409 |issue=30 |pages=6989–6997 |doi=10.1007/s00216-017-0572-7|pmid=29147747 |s2cid=24611076 }}
References
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